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You Are What You Wear

Buying New Clothes to Join a Startup

Why you should care

Because the best view of what’s happening on the inside often comes from the outside.

I’ve never been a good dresser. My wife, Haley, will tell you that on our early dates, I arrived looking less like a suave stud and more like a homeless man stumbling into a restaurant.

But here’s the thing: It’s not my fault. My life has almost always been about work, and my work has always had a uniform. When I was a war reporter, I had the obligatory tan vest and an endless supply of crisp, button-down blue shirts. When I was a speechwriter, I had the go-to rotation of suits and ties. Neither made for hip date-wear, so in those moments, I had to freestyle. Hence the problem.

When I walked into the office, I got laughed at. Twice.

But then I joined a startup in Silicon Valley (this one). And I have to admit: Techies have, perhaps, the most ridiculous uniform of all.

As I prepared to on-board (a phrase that — before starting this job — I never knew existed), I got the same piece of advice from every person I knew in the Valley. It was advice dispensed with particular force to those coming from the East Coast: “Be. Careful. What. You. Wear.”

In the startup world, crisp button-down shirts are for those who are trying too hard; tailored suits are for those who take themselves too seriously; and anyone who looks like they might come from 1990s corporate culture gets unceremoniously ridiculed.

No joke. We had a big interview recently at OZY, so I decided to wear a suit. Seems logical, right? It wasn’t. When I went to get breakfast, I got my coffee with a side of “what-are-you-wearing” stares. When I walked into the office, I got laughed at. Twice.

What could a startup culture present that would be truly new? A lot more than slim-fitting pants.

So before I showed up in Mountain View, California, I went to Macy’s in search of the wardrobe that techies have made mainstream: the button-down shirt with brightly colored stripes or big boxes; the cool-kid casual vest that zips in the front; the shoes that are trendy without trying — you know, the ones that don’t have shoelaces, or if they do, are leather shoes with shoelaces.

It was awful. It was exhausting. I eventually gave up and let Haley do the choosing.

But survive I did. And with startup uniform in hand, I arrived at OZY with big ambitions and an even bigger hope that the worst of my adjustment period was behind me. I’d been all over the world as a reporter. I’d worked for the president. What could a startup culture present that would be truly new? A lot more than slim-fitting pants.

On my first day, I met what quickly became the dorky friend you like hanging out with, but are always embarrassed to know. He’s called The Whiteboard.

The Whiteboard sits in every office, seductively empty, a canvas waiting for a brilliant idea to be circled and then linked with purposeful lines to even more brilliant ideas. Before The Whiteboard gets erased, it gets photographed — catalogued for the next time a meeting is called to answer the question “What makes us … us?” That’s actually written on The Whiteboard next to me right now.

Then there are the meetings. Out here, the first step is always a step back. And the last step is to always ponder what step we’re missing — a command that inevitably leads to an awkward silence while everyone who’s spent the past hour texting or typing looks up to the sky, squints their eyes, and pretends to think hard. After 10 seconds, some sacrificial soul offers up an answer so that everyone else can go back to filling out that latest BuzzFeed quiz.

In most places, a good idea is met with ‘Yes … but here are the reasons it can’t work.’ Out here, a good idea is met with ‘Yes … and now go do it.’

Then there’s the jargon, which seeps into the language center of your brain when you’re not even looking. There’s the worth-repeating “on-boarding.” There’s “bandwith” and ”interface.” They’ve even messed with “success” — which, it turns out, no longer means something you aspire to over the course of a career; instead, it’s something you seek in every action. When Haley and I recently decided to remodel our kitchen, my first question was, “What does success look like?” Her answer: “A better kitchen.”

So it’s been an adjustment. Joining a startup is not for the faint of heart. And it shouldn’t be. But at least you’ve got friends to do it with — namely, The Whiteboard (just don’t tell anyone else we’re friends). More importantly, the thing that makes a startup unique from almost anything else out there is that you are building something from the ground up. And there’s nothing else like that.

In most places, a good idea is met with “Yes … but here are the reasons it can’t work.” Out here, a good idea is met with “Yes … and now go do it.” Most of us have jobs with total direction and very little creative ability to question the big stuff. Out here, you have to question the big stuff — because all that matters is what works.

Those first steps through the door at your first startup are overwhelming. In an instant, 10 different ideas and 20 different tasks are coming your way. But a few weeks in, when you take a step back and define success, when you really imagine the big, purposeful company you will one day become, it’s a pretty inspiring moment. And it almost makes wearing this geeky striped shirt totally worth it.

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Meet The Author Aneesh Raman

Aneesh Raman is a Senior Editor at OZY. A former Middle East Correspondent for CNN and speechwriter for President Obama, Raman tends to identify himself first as a proud member of Red Sox nation.

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